喹啉正离子,4-碘-1-甲基-,碘化 | 16560-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 喹啉正离子,4-碘-1-甲基-,碘化
• 英文名称: N-methyl-4-iodoquinolinium iodide
• 英文别名: 4-iodo-1-methyl-quinolinium; iodide；4-Jod-1-methyl-chinolinium; Jodid；4-Iodo-1-methylquinolin-1-ium;iodide
• CAS: 16560-44-4
• 化学式: C₁₀H₉IN*I
• 分子量: 396.997
• InChiKey: RCLRJEFKAMUKLM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-环己二酮 、 喹啉正离子,4-碘-1-甲基-,碘化 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以42%的产率得到2-(1-methylquinolin-4(1H)-ylidene)cyclohexane-1,3-dione
  参考文献：
  名称：

  在喹啉的C2，C3和C4处进行官能化：发现具有溶剂变色和pH敏感特性的C3喹啉鎓衍生物的水溶性甜菜碱染料

  摘要：

  在喹啉的C2，C3和C4官能化过程中，我们遇到了一步法合成金属的甜美碱甜菜碱染料的C3喹啉鎓衍生物。一些Mesomeric甜菜碱染料具有溶剂变色性质，并且对pH值和水中的溶剂化物敏感。某些甜菜碱染料在酸性和碱性环境下具有不同的特性；pH值的变化会导致染料的黄色（中性或碱性）和无色（酸性）之间可逆的相互转化。在存在环糊精的情况下染料的紫外线吸收强度的变化表明环糊精和染料之间形成了包合物。由于分子中存在正电荷和负电荷，甜菜碱染料部分溶解在水中。这些甜菜碱染料不具有细胞毒活性，

  DOI：

  10.1016/j.dyepig.2020.108341
• 作为产物：
  描述：

  4-羟基喹啉 在 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 喹啉正离子,4-碘-1-甲基-,碘化
  参考文献：
  名称：

  Twisted Cyanines: A Non-Planar Fluorogenic Dye with Superior Photostability and its Use in a Protein-Based Fluoromodule

  摘要：

  The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named alpha-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that alpha-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. alpha-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that alpha-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of alpha-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. alpha-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new alpha-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that alpha-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.

  DOI：

  10.1021/ja308629w

文献信息

• New Cyanine–Oligonucleotide Conjugates: Relationships between Chemical Structures and Properties
  作者：Rémy Lartia、Ulysse Asseline

  DOI：10.1002/chem.200500908

  日期：2006.3.1

  range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines, the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5'-end or to an internucleotidic phosphate. In the first

  由于单甲胺花菁-寡核苷酸2'-脱氧核糖核苷酸（ODN）共轭物的化学结构对其结合和荧光性质的影响仍未确定，因此我们合成并研究了多种具有各种结构模式的共轭物。获得了不同的花青染料，例如硫氰酸，喹啉和噻唑橙的异构体。对于不对称花青，连接子连接到喹啉或苯并噻唑核上。ODN对应物的影响通过将花青素连接到5'端或核苷酸间磷酸进行评估。在第一种情况下，研究了相邻核酸碱基的影响，而在第二种情况下，研究了带有花青的磷原子处的立体化学构型。我们在这里报告染料和缀合物的结构及其某些特性之间的关系，例如在与目标序列杂交时观察到的稳定性和荧光变化。这项研究为ODN-花青共轭物的设计提供了有用的信息。
• 1-benzopyrane-derivatives and colouring agents containing the salts thereof
  申请人：——

  公开号：US20030196281A1

  公开（公告）日：2003-10-23

  The present invention concerns an agent for coloring fibers that is obtained by mixing two components—if necessary with the addition of an alkalinizing agent or an acid—said agent being characterized in that one component (component A2) contains at least one electrophilic compound and the other component (component A1) contains at least one 1-benzopyran of formula (Ia)/(Ib) or a 1-benzopyrylium derivative of formula (I), 1 and a method for temporarily coloring keratin fibers whereby the hair is first colored with the aforesaid coloring agent and then, at any future time, is again decolorized with a reducing agent.

  本发明涉及一种纤维着色剂，该着色剂由两种组分混合而成，必要时加入碱化剂或酸，其特征在于其中一种组分（组分 A2）含有至少一种亲电化合物，另一种组分（组分 A1）含有至少一种式 (Ia)/(Ib) 的 1-苯并吡喃或式 (I) 的 1-苯并吡喃衍生物、 1 以及一种对角蛋白纤维进行临时着色的方法，首先用上述着色剂对头发进行着色，然后，在以后的任何时间，再用还原剂对头发进行脱色。
• 215. Preparation of 4′-cyanines
  作者：Frances M. Hamer

  DOI：10.1039/jr9390001008

  日期：——
• Brydowna, Roczniki Chemii, 1932, vol. 12, p. 89,96
  作者：Brydowna

  DOI：——

  日期：——
• Dye compositions containing quinolinium salts
  申请人：——

  公开号：US20030177592A1

  公开（公告）日：2003-09-25

  The dye composition (A) for dyeing fibers, especially keratin fibers, such as human hair, is made by mixing a first component (A1) and a second component (A2) and adding an alkalizing agent or an acidifying agent, as needed. The second component (A2) consists of at least one compound with a nucleophilic reaction center and the first component (A1) consists of at least one 1-alkyl quinolinium derivative of formula (Ia) or (Ib): 1 A multicomponent kit consisting of the first and second components packaged separately is also described as well as a method of dyeing fibers using the multicomponent kit.